I recently had a reader email this question, and thought it would make for a good blog post:

While we're happy to conduct single-item inspections to troubleshoot problems exactly like this, this particular situation is so common that it probably doesn't need an inspection. The stains on the siding are the result of moisture; that much is for certain. When water runs through the wood and wall sheathing, it picks up tannins in the wood and leaves dark stains on the siding. If the home experiences ice dams and the stains start at the soffits and run down the siding, they're probably the result of water leaking through the roof as a result of the ice dams. The illustration below from The Ice Dam Company shows the path of the water.

Here's an extreme example of what you might see on the side of the wall during the winter:

Here's a close-up photo showing some ice turned brown from the tannins in the wood:

Here are a couple of photos showing what stained siding looks like after all the ice is gone.



So ice dams are one possibility. In this particular case, I got a little more information from the homeowner and decided the stains probably weren't the result of ice dams. When stains also show up on gable walls, they definitely aren't the result of ice dams.
When siding stains appear in random areas during the winter, it's the result of moisture migrating through the walls during very cold weather, condensing as frost, then melting again once the outdoor temperature warms up. That's the long and short of it, but there are a number of things that will increase the potential for water stains to show up on siding.

Cold Weather
The colder it is outside, the greater the potential for frost accumulation in the walls and attic. When there is an extended period of unusually cold weather like we had last winter, the potential for frost accumulation will increase as well.